Evaluation of 3,3′-Triazolyl Biisoquinoline N,N′-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane

A new class of axial-chiral biisoquinoline N,N′-dioxides was evaluated as catalysts for the enantioselective hydrosilylation of acyl hydrazones with trichlorosilane. While these catalysts provided poor to moderate reactivity and enantioselectivity, this study represents the first example of the orga...

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Autores principales: Sun, Shiyu, Xu, Changgong, Jarvis, Jamielyn, Nader, Phillip, Naumann, Brandon, Soliven, Abigail, Peverati, Roberto, Takenaka, Norito
Formato: Online Artículo Texto
Lenguaje:English
Publicado: 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9589403/
https://www.ncbi.nlm.nih.gov/pubmed/36285183
http://dx.doi.org/10.3390/catal11091103
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author Sun, Shiyu
Xu, Changgong
Jarvis, Jamielyn
Nader, Phillip
Naumann, Brandon
Soliven, Abigail
Peverati, Roberto
Takenaka, Norito
author_facet Sun, Shiyu
Xu, Changgong
Jarvis, Jamielyn
Nader, Phillip
Naumann, Brandon
Soliven, Abigail
Peverati, Roberto
Takenaka, Norito
author_sort Sun, Shiyu
collection PubMed
description A new class of axial-chiral biisoquinoline N,N′-dioxides was evaluated as catalysts for the enantioselective hydrosilylation of acyl hydrazones with trichlorosilane. While these catalysts provided poor to moderate reactivity and enantioselectivity, this study represents the first example of the organocatalytic asymmetric reduction of acyl hydrazones. In addition, the structures and energies of two possible diastereomeric catalyst–trichlorosilane complexes (2a–HSiCl(3)) were analyzed using density functional theory calculations.
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spelling pubmed-95894032022-10-24 Evaluation of 3,3′-Triazolyl Biisoquinoline N,N′-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane Sun, Shiyu Xu, Changgong Jarvis, Jamielyn Nader, Phillip Naumann, Brandon Soliven, Abigail Peverati, Roberto Takenaka, Norito Catalysts Article A new class of axial-chiral biisoquinoline N,N′-dioxides was evaluated as catalysts for the enantioselective hydrosilylation of acyl hydrazones with trichlorosilane. While these catalysts provided poor to moderate reactivity and enantioselectivity, this study represents the first example of the organocatalytic asymmetric reduction of acyl hydrazones. In addition, the structures and energies of two possible diastereomeric catalyst–trichlorosilane complexes (2a–HSiCl(3)) were analyzed using density functional theory calculations. 2021-09 2021-09-14 /pmc/articles/PMC9589403/ /pubmed/36285183 http://dx.doi.org/10.3390/catal11091103 Text en https://creativecommons.org/licenses/by/4.0/This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Sun, Shiyu
Xu, Changgong
Jarvis, Jamielyn
Nader, Phillip
Naumann, Brandon
Soliven, Abigail
Peverati, Roberto
Takenaka, Norito
Evaluation of 3,3′-Triazolyl Biisoquinoline N,N′-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane
title Evaluation of 3,3′-Triazolyl Biisoquinoline N,N′-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane
title_full Evaluation of 3,3′-Triazolyl Biisoquinoline N,N′-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane
title_fullStr Evaluation of 3,3′-Triazolyl Biisoquinoline N,N′-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane
title_full_unstemmed Evaluation of 3,3′-Triazolyl Biisoquinoline N,N′-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane
title_short Evaluation of 3,3′-Triazolyl Biisoquinoline N,N′-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane
title_sort evaluation of 3,3′-triazolyl biisoquinoline n,n′-dioxide catalysts for asymmetric hydrosilylation of hydrazones with trichlorosilane
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9589403/
https://www.ncbi.nlm.nih.gov/pubmed/36285183
http://dx.doi.org/10.3390/catal11091103
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